EXERCCIOS P3 2011

1.A oxidao de HOCH2CH2CHO com cido crmico produz: a) HOCH2CH2CHO2H b) HO2CCH2CHO c)HO2C CH2CO2H d) HOCCH2CO2H e)nenhuma das anteriores 2. A oxidao de ___ com oznio, com subsequente tratamento com redutor (Zn), gera, como nico produto, o 1,5 pentanodial a)1,5-pentanodiol b)2,4-pentanodiona c)ciclopenteno d)ciclopentano e)nenhuma das anteriores 3. Uma nitrao eletroflica aromtica envolve: a)NO+ b)NO2+ c)NO3+ d)NO2 e)nenhuma das anteriores 4. O cido carboxlico mais forte o: a) cido 2-coloactico b) cido 2,2-dicloroactico c)cido 2-bromoactico d)cido 2-iodoactico 5-Uma limitao da reao de alquilao de Friedel-Crafts : a)rearranjo de carboctions b)a reao do benzeno com o cido de Lewis c)a reao do benzeno com cido de Lewis d)a formao de diversas subsitituies no anel e)nenhuma das anteriores 6. Cloreto de butilmagnsio reage com dixido de carbono e gera a)lcool butlico b)cido butrico c)cloreto de butila d)nion pentanoato e)nenhuma das anteriores 7. A vantagem da acilao de Friedel-Crafts reside em a)completa ocorrncia de rearranjo b)formao de composto poliacilados c)ser desnecessrio usar catalisador d)nenhuma das anteriores 8. Benzeno reage com Br+ porque Br+ : a)um nuclefilo b)um radical c)um eletrfilo d)um bromfilo e)nenhuma das anteriores 9-O grupo carboxila do cido benzico dirige o eletrfilo para a posio: a)orto b)meta c)para d)orto e para e)nenhuma das anteriores 10. cido benzico pode ser preparado pela oxidao: a) de um grupo CN ligado ao benzeno b)de um grupo OH ligado ao benzeno c)de um grupo NH2 ligado ao benzeno d)nenhuma das anteriores

11- O grupo cloro, no clorobenzeno, dirige o eletrfilo para a posio a)orto,apenas b)meta c)para, apenas d)orto, meta e para e)nenhuma das anteriores 12-Qual material mais reativo em reao com nuclefilos? a)acetaldedo b)acetona c)1,1,3,3 tetrametilpropanona d)1,1,1,3,3,3-hexametillpropanona 13. Grupo meta dirigente______ de reao de S8Ar a)aumentam velocidade b)diminuem velocidade c)no afetam velocidades 14. Nas S8Ar o grupo H2N- na anilina um substituinte a)ativante b)desativante c)nem ativante nem desativante d)meta dirigente e)nenhuma das anteriores 15. A sulfonao do benzeno envolve a)SO+ b)SO2+ c)SO3+ d)SO3e)nenhuma das anteriores 16. _________ desativante e orto/para dirigente em a)NO2 b)OH c)H d)Cl

17. O que a oxidao de 1propanol com cido crmico gera? a)um lcool b)um aldedo c)uma cetona d)um cido e)nenhuma das anteriores 18- O que a hidratao catalisada por cido do cliclodecino produz? a)ciclodecanona b)cliclodecadieno c)ciclodecanodiol d)ciclodecanodial e)nenhuma das anteriores 19-Quando o on cianeto reage com uma cetona forma-se a)um cido b)um halo-hidrina c)um aldido d)uma amina e)nenhuma das anteriores 20-O que a oxidao de 1-propanol com cido crmico, em acetona, gera a)um lcool b)um aldido c)uma cetona d)um cido e)nenhuma das anteriores 21-Dimetilamina reage com uma cetona e produz a)amida b)imida c)amina d)enamina e)nenhuma das anteriores 22-Nitrilas so hidrolisveis a a)lcoois b)teres c)enaminas

d)amidas e)nenhuma das anteriores 23-Bons grupos de partida, em reaes de grupos acila, so a)bases fortes b)bases fracas c)cido fortes d)cidos fracos e)nenhuma das anteriores 24- Cloretos de cidos tratados com aminas secundrias do: a)cidos b)amidas c)iminas d)nenhuma reao 25- Brometo de propanoila reage com acetato de sdio para dar: a) anidrido actico b) anidiro propinico c) propionato de etilal d) todos acima e) nenhuma das anteiores 26- Amnia reage com aldido e produz a) lcool b) amida c) imina d) amina e) nenhuma das anteriores

oxignio/sada de gua c)protonao do oxignio/ataque do nitrognio ao carbono/transferncia do H+ ao oxignio/sada de gua formando ction no N/sada de H+ d)nenhuma das anteriores 28-Controle cintico se refere a)formao do produto mais estvel b)formao mais rpido do produto menos estvel c)formao de produtos em velocidades diferentes d)energia liberada no processo e)nenhuma das anteriores 29-Todas as ligaes entre carbonos no benzeno a)so iguais b)tem comprimento alternados c)So duplas d)So deslocalizadas e)nenhuma das anteriores 30- Controle termodinnico se refere a)quantidade de energia liberada b)formao preferencial de produto mais estvel c)formao do intermedirios mais instvel d)quantidade de calor liberada e)nenhuma das anteriores 31-Anidridos so hidrolisados a)mais rapidamente que amidas b)mais lentamente que steres c)na mesma velocidade que cloretos cidos d)nenhuama das anteriores 32-O nome comum do hidroxibenzeno a)anilina

27- As etapas mecansticas mecansticas de um Ads de anubas primrias ao grupo carbonila em meio cido, ~soa: a)protonao da amina/ataque de on ao carbono/transferncia do H+ ao oxignio/sada de gua b) protonao do oxgnio/ataque do nitrognio ao carbono/transferncia do H+ ao

b)cido benzico c)fenol d)benzol e)nenhuma das anteriores

(c) CH2 CH2 (d) CH3OCH3 9. One mole of NaBH4 reacts with 1 mole of acetone, CH3C(O)CH3, to give, after treatment with aqueous acid, (a) an acid (b) a ketone (c) an alcohol (d) hydrogen 10. LAH reacts with glyoxal, HC(O)C(O)H, to give (a) CH3CO2H (b) HOCH2CH2OH (c) H2C CH2 (d) HOCH2CO2H 11. LAH reacts with H2C CHC(O)H to give (a) CH3CH2C(O)H (b) CH3CH2CH2OH (c) H2C CHCO2H (d) H2C CHCH2OH 12. Hydrogen (H2), in the presence of Raney Ni catalyst, reacts with H2C CHCHO to give (a) CH3CH2CHO (b) CH3CH2CH2OH (c) H2C CHCO2H (d) H2C CHCH2OH 13. CH3CHO reacts first with ethyllithium (CH3CH2Li) and then with dilute acid to give (a) ethane (b) butan-2-ol (c) butane (d) no reaction 14. Lithium reacts with n-butyl chloride to give (a) n-butane (b) n-butyllithium (c) chlorine (d) hydrogen 15. Formaldehyde (HCHO) reacts first with CH3MgCl and then with dilute acid to give a (a) primary alcohol (b) secondary alcohol (c) tertiary alcohol (d) quaternary alcohol 16. The oxidation of CH3CH2OH with acidic dichromate (Cr2O 2

CHAPTER 13 Alcohols
1.Alcohols have boiling points than do alkanes of similar molecular weight. (a) lower (b) higher (c) similar 314 2. The formal (IUPAC) names for alcohols end in (a) -al (b) -ol (c) -one (d) ane 3. Glycols have hydroxyl group(s). (a) one (b) two (c) three (d) four 4. Alcohols can act as acids. (a) True (b) False 5. Alcohols can act at bases. (a) True (b) False 6. Alcohols react with active metals (Na, K, etc.) to produce gas. (a) oxygen (b) hydrogen (c) nitrogen (d) helium 7. The formation of ethylene glycol (HOCH2CH2OH) from ethylene (H2C CH2) is an example of (a) oxidation (b) reduction (c) dehydration (d) hydrogenation 8. An example of a compound that contains a carbonyl group is (a) H2C O (b) CH3OH

7 )gives

(a) a ketone (b) ethyl alcohol (c) an aldehyde (d) an acid 17. CH3CH2OH reacts with pyridinium chlorochromate (PCC) to give (a) a ketone (b) an alcohol (c) an aldehyde (d) an acid 18. PBr3 reacts with ethanol to give (a) tribromoethane (b) bromoethanol (c) bromoethane (d) no reaction 19. Thionyl chloride, ClS(O)Cl, reacts with isopropyl alcohol,(CH3)2CHOH, to give (a) 2-chloropropane (b) 1-chloropropane (c) 2-propanol (d) acetone (a ketone) 20. Isopropyl alcohol, (CH3)2CHOH, reacts with hot concentrated H2SO4 to give (a) propane (b) 2-propanol (c) propene (d) propyne

(c) conjugation (d) all of the above 4. sp2 orbitals form stronger bonds than sp3 orbitals because the orbitals (a) hold electrons further from the nucleus (b) have more p character (c) have more s character (d) are not hybridized 5. Bonding MOs are the AOs they are made from. (a) more stable than (b) less stable than (c) equal in stablity to 6. MOs are classified as (a) nonbonding (b) antibonding (c) bonding (d) all of the above 7. Nonbonding MOs antibonding MOs. (a) are equal in stability to (b) are less stable than (c) are more stable than (d) have no energy relationship with 356 8. The lowest energy MO has nodes. (a) zero (b) one (c) two (d) three 9. The s-cis structure refers to (a) configuration around a double bond (b) conformation around a single bond (c) configuration around an alkene bond (d) configuration around an alkyne bond 10. The addition of 1 mol of HBr to 1 mol of 1,3-butadiene gives constitutional isomers. (a) zero (b) one

CHAPTER 16 Conjugated Systems 1.Conjugated dienes contain (a) only two double bonds (b) two double bonds connected to the same carbon atom (c) alternating single and double bonds (d) two double bonds separated by two single bonds 2. Conjugated double bonds nonconjugated double bonds. (a) have greater stability than (b) have less stability than (c) have no relationship to the stability of (d) have equal stability to 3. Resonance energy results from (a) sharing electrons (b) overlapping p orbitals

(c) two (d) four 11. Aprimary allylic carbocation is less stable than acarbocation. (a) methyl (b) vinyl (c) secondary alkyl (d) tertiary alkyl 12. Kinetic control refers to (a) formation of the most stable product (b) the stability of reactants relative to products (c) how fast a product forms (d) the amount of potential energy an atom has 13. Thermodynamic control refers to (a) how fast a product forms (b) the amount of kinetic energy an atom has (c) formation of the most stable (lowest energy) product (d) control of the movement of heat 14. An allyl radical has (a) an unpaired electron localized on one atom (b) an unpaired electron delocalized on two atoms (c) a positive charge localized on one atom (d) a negative charge delocalized on two atoms 357 15. ADielsAlder reaction is called a (4+2) cycloaddition reaction because (a) four bonds react with two bonds (b) four molecules react with two molecules (c) four pi electrons interact with two pi electrons (d) four pi electrons interact with two sigma electrons 16. The requires an s-cis conformation to undergo a Diels Alder reaction. (a) diene (b) dienophile

(c) monoene (d) allyl carbocation 17. The DielsAlder reaction is (a) isotopic (b) stereophonic (c) stereospecific (d) isothermal 18. HOMO refers to (a) an unemployed person (b) high-order molecular orbital (c) highest occupied molecular orbital (d) a homosapien 19. LUMO refers to (a) luxurious sedan driven by a chauffeur (b) lowest unoccupied molecular orbital (c) a rock band (d) lowest unimolecular orbital 20. An exo position refers to (a) annex a position (b) being outside (c) being inside (d) a position that no longer exists CHAPTER 17 Aromatic Compounds 1. Aromatic compounds are (a) alkanes (b) linear (c) nonconjugated and cyclic (d) conjugated and cyclic 2. Ortho refers to groups that are to each other. (a) 1,1(b) 1,2(c) 1,3(d) 1,43. The common name for hydroxybenzene is (a) aniline (b) benzoic acid (c) phenol (d) fenol 4. All bond lengths in benzene (a) are equal

(b) alternate in length (c) are all different lengths (d) cannot be measured 5. Benzene is more stable than (a) cyclohexene (b) cyclohexane (c) 1,3-cyclohexadiene (d) all of the above 6. Annulenes are (a) linear compounds (b) conjugated cyclic compounds (c) conjugated linear compounds (d) annual events 7. The MO description of benzene has different energy levels. (a) two (b) three (c) four (d) six 8. 1,3-Cyclobutadiene is (a) aromatic (b) nonaromatic (c) antiaromatic (d) nonconjugated 9. 1,3,5,7-Octatetraene is (a) a cation (b) an anion (c) a diradical (d) a 10-membered ring 10. A Frost circle is used to predict (a) AO energy levels (b) condensation temperatures (c) MO energy levels (d) freezing points 11. Aromatic six-membered rings are nonaromatic sixmembered ring. (a) more stable than (b) less stable than (c) equal in stability to 12. Each ring atom in an aromatic compound contains (a) two hydrogen atoms

(b) a p orbital (c) an sp3 orbital (d) at least three p orbitals 13. Huckels rule predicts aromaticity for a conjugated ring with electrons. (a) one (b) three (c) four (d) six 14. Pyridine is aromatic because its nonbonding electrons (a) are included in the electron system (b) are not included in the electron system (c) are unpaired (d) are removed from the molecule 15. The cyclopropenyl cation has electrons. (a) one (b) two (c) three (d) four 16. The cyclopentadienyl anion has electrons. (a) two (b) four (c) six (d) eight CHAPTER 18 Reactions of Benzene
4

1. The intermediate in an electrophilic substitution reaction is (a) an anion (b) a radical (c) an unpaired electron (d) a carbocation 01 2. Benzene reacts with Br+ because Br+ is (a) a nucleophile (b) a radical (c) an electrophile (d) a bromophile 3. The addition of an electrophile to benzene gives (a) a non-allylic carbocation

(b) an aromatic carbocation (c) a diallyl carbocation (d) an aromatic anion 4. An electrophilic nitration substitution reaction involves (a) NO+ (b) NO2+ (c) NO3+ (d) NO2 5. A sulfonation electrophilic substitution reaction involves (a) SO+ (b) SO2+ (c) SO3+ (d) SO3 6. The best FriedelCrafts alkylating agents are carbocations. (a) primary (b) secondary (c) tertiary (d) quaternary 7. A limitation of FriedelCrafts alkylation reactions is (a) rearrangement reactions (b) adding deactivating groups to the benzene ring (c) spontaneous reactions without a Lewis acid (d) multiple acylation reactions 8. An advantage of FriedelCrafts acylation reactions is that (a) rearrangement reactions readily occur (b) trialkylbenzenes are easily made (c) spontaneous reactions occur without a Lewis acid (d) multiple acylation reactions do not readily occur 9. Nucleophilic substitution reactions require a benzene ring to have (a) strong electron-donating groups (b) no substituents (c) strong electron-withdrawing groups (d) strong o/p-directing groups 10. Benzyne is a molecule with (a) all single bonds (b) all double bonds (c) three single bonds and three double bonds (d) one triple bond

11. The amino (H2N ) group in aniline is substituent. (a) an activating (b) a deactivating (c) neither an activating nor a deactivating (d) a meta-directing 12. A Clemmensen reduction reaction (a) converts a ketone into an aldehyde (b) oxidizes an alcohol to a carboxylic acid (c) reduces a ketone to an alcohol (d) reduces a carbonyl group to a methylene ( CH2 ) group 13. A benzoic acid can be prepared by oxidizing substitutent on a benzene ring. (a) a hydroxyl (b) an amino (c) a primary alkyl (d) a tertiary alkyl 14. Benzene can be reduced by reaction with in the presence of a catalyst. (a) hydrogen (b) oxygen (c) nitrogen (d) helium 15. An inductive effect refers to the movement of electrons through (a) bonds (b) p orbitals (c) nonpolar bonds (d) sigma bonds 16. Meta-directing groupsof electrophilic substitution reactions. (a) increase the rates (b) decrease the rates (c) do not affect the rates 17. is deactivating and ortho/para directing. (a) NO2 (b) OH (c) H (d) Cl 18. The carboxylic acid group in benzoic acid directs the incoming electrophile to the position(s). (a) ortho (b) meta

(c) para (d) ortho and para 19. The nitro group in nitrobenzene directs the incoming electrophile to the position(s). (a) ortho (b) meta (c) para (d) ortho and para 20. The chloro group in chlorobenzene directs the incoming electrophile to the position(s). (a) ortho (b) meta (c) para (d) ortho and para CHAPTER 19 Aldehydes and Ketones 1. The formal name for aldehydes ends in (a) -one. (b) -ide (c) -al. (d) ane 2. The formal name for ketones ends in (a) -ane (b) -ide (c) -al (d) one 3. Aldehydes have boiling points than/as alcohols of comparable molecular weight. (a) higher (b) lower (c) about the same 4. Acetone is the common name for (a) 1-butanone (b) 1-propanone (c) 2-propanone (d) 2-butanone 5. Which material is most reactive toward nucleophilic addition? (a) acetaldehyde (b) dimethyl ketone (c) diisopropyl ketone (d) di-ter t-butyl ketone 6. The oxidation of 1-propanol with chromic acid yields (a) an alcohol (b) an aldehyde (c) a ketone

(d) an acid 428 7. The oxidation of 2-propanol with chromic acid yields (a) an alcohol (b) an aldehyde (c) a ketone (d) an acid 8. The oxidation of 1-propanol with PCC gives (a) an alcohol (b) an aldehyde (c) a ketone (d) an acid 9. The oxidation of with ozone followed by reduction with (CH3)2S yields one product, 1,5pentanedial. (a) 1,5-pentanediol (b) 2,4-pentanedione (c) cyclopentene (d) cyclopentane 10. The acid-catalyzed hydration of cyclodecyne yields (a) cyclodecanone (b) cyclodecadiene (c) cyclodecanediol (d) cyclodecanedial 11. Reduction of acetic acid with Li(tri-ter t -butoxy)AlH yields (a) an acid (b) an aldehyde (c) an alcohol (d) a ketone 12. The reaction of acetyl chloride with excess Grignard reagent followed by acidification yields (a) a ketone (b) an ester (c) a secondary alcohol (d) a tertiary alcohol 13. Lithium dimethylcuprate (Gilman reagent) reacts with acetyl chloride to give (a) a ketone (b) an ester (c) a secondary alcohol (d) a tertiary alcohol 429 14. The cyanide ion C N reacts with a ketone to give

(a) an acid (b) a cyanohydrin (c) an aldehyde (d) an amine 15. The acid-catalyzed addition of water to formaldehyde gives (a) a ketal (b) a hemiacetal (c) an acetal (d) a hydrate 16. The acid-catalyzed addition of 2 mol of alcohol to 1 mol of aldehyde yields (a) a ketal (b) a hemiacetal (c) an acetal (d) a hydrate 17. Ammonia reacts with an aldehyde to give an (a) alcohol (b) amide (c) imine (d) amine 18. The reaction of a Wittig reagent with ketones give (a) alkenes (b) ketones (c) aldehydes (d) alkanes 19. Silver ion, Ag+, reacts with aldehydes to form (a) a red precipitate (b) a silver mirror (c) a blue solution (d) there is no reaction 20. Dimethylamine reacts with a ketone to give an (a) amide (b) imide (c) amine (d) enamine

445 2. -Bromobutyric acid is also called (a) 1-bromobutanoic acid (b) 2-bromobutanoic acid (c) 2-bromobutanoate acid (d) 3-bromobutanoic acid
3. The magnesium salt of acetic acid is called magnesium (a) formate (b) acetate (c) ethanoic acid (d) acetic acid 4. is most soluble in water. (a) Sodium octanoate (b) Octanoic acid (c) Sodium decanoate. (d) Decanoic acid 5. The strongest acid is (a) 2-chloroacetic acid (b) 2,2-dichloroacetic acid (c) 3-chloroacetic acid (d) 2,3-dichloroacetic acid 6. The strongest acid is (a) p-nitrobenzoic acid (b) m-nitrobenzoic acid (c) p-hydroxybenzoic acid (d) m-hydroxybenzoic acid 7. Chromic acid oxidation of HOCH2CH2CHO gives (a) HOCH2CH2CO2H (b) HO2CCH2CHO (c) HO2CCH2CO2H (d) HOCH2CH2CHO 8. Potassium permanganate oxidation of 3-hexene gives (a) potassium propionate (b) potassium hexanate (c) potassium acetate (d) potassium ethanoate 9. Chromic acid oxidation of isobutylbenzene gives (a) benzoic acid (b) dimethylbenzoic acid (c) isopropylbenzoic acid (d) no reaction 10. Butylmagnesium chloride reacts with carbon dioxide to give (a) butyl alcohol (b) butyric acid

CHAPTER 20 Carboxylic Acids

1.Cyclohexanetricarboxylic acid contains carboxylic acid groups. (a) one (b) two (c) three (d) four

(c) butyl chloride (d) pentanoate anion 11. Reaction of 2-methylpropanoic acid with LAH gives (a) ethylene glycol (b) 1,3-butylenediol (c) 2-methyl-1,2-propanediol (d) 2-methylpropanol

7. Acetic acid reacts with propionic acid to give anhydride(s). (a) acetic (b) propionic (c) acetic propionic (d) all of the above 8. Propionyl bromide reacts with sodium acetate to give anhydride( s). (a) acetic (b) acetic propionic (c) propionic (d) all of the above 9. Esters are made from the reaction between (a) carboxylic acid molecules (b) alcohol molecules (c) alcohol and carboxylic acid molecules (d) anhydride and water molecules 10. The self-condensation reaction of one molecule of 5-hydroxyhexanoic acid gives (a) an anhydride (b) a lactone (c) a ketone (d) a lactam 11. Ethyl acetate is hydrolyzed by water to give (a) a lactone (b) an ester (c) an anhydride (d) a carboxylic acid and an alcohol 12. Anhydrides are hydrolyzed esters. (a) faster than (b) slower than (c) at the same rate as 13. The reaction of excess ethyl acetate with diethylamine gives an (a) amide (b) imide (c) anhydride. (d) amino acid 14. The reaction of excess acetyl chloride with ethylamine gives an

CHAPTER 21 Carboxylic Acids

1. An inductive effect involves (a) the withdrawal of electrons through sigma bonds (b) the donation of electrons through sigma bonds (c) the withdrawal and donations of electrons through sigma bonds (d) all of the above 2. Good leaving groups in acyl transfer reactions are (a) strong bases (b) weak bases471 (c) strong acids (d) weak acids 3. Acid halides are esters. (a) more reactive than (b) less reactive than (c) of equal reactivity to 4. Acid chlorides react with (a) alcohols (b) amines (c) carboxylic acids (d) all of the above 5. Acid chlorides react with secondary amines to give (a) acids (b) amides (c) imides (d) no reaction 6. Acid chlorides are reduced to with LAH. (a) carboxylic acids (b) alcohols (c) ketones (d) aldehydes

(a) amide (b) imide (c) anhydride (d) amino acid 15. The reduction of acetamide, CH3C(O)NH2, with LiAlH4 gives an (a) carboxylic acid (b) amide (c) alcohol (d) amine 16. The self-condensation of one molecule of 5-aminopentanoic acid gives (a) a lactam (b) an ester (c) an amide (d) a lactone 17. Imides are acidic than amides. (a) more (b) less 473 18. Nitriles are hydrolyzed to (a) alcohols (b) lactones (c) imides (d) amides and acids 19. Nitriles are reduced to (a) alcohols (b) carboxylic acids (c) amines (d) amides